


Are we still acting ?

by Kit_Cat03



Category: Critical Role (Web Series)
Genre: Adorable Jester Lavorre, Alternate Universe - Modern Setting, Caleb Widogast Deserves Nice Things, Caleb Widogast Needs a Hug, F/M, Jester Lavorre & Caleb Widogast Friendship, Jester Lavorre Needs a Hug
Language: English
Status: In-Progress
Published: 2020-07-16
Updated: 2020-08-22
Packaged: 2021-03-05 00:55:07
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 7
Words: 14,631
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25305604
Author URL: https://archiveofourown.org/users/Kit_Cat03/pseuds/Kit_Cat03
Summary: Marrion is delighted to her that Jester has found herself an amazing boyfriend. She's coming to visit and cant wait to meet him. Only Jester made him all up to make her mother happy. Her roommate Beau gots her covered though getting her nerdy friend Caleb to pretend to be this mysterious new boyfriend of hers. Jesters and Caleb's friendship grows as they try to convince her mother they are a couple happily in love. Though as the deep they get into these the line between acting and reality seems to blur.A Modern AU of the mighty nine in college. Jester getting herself stuck in a sticky situation trying to impress her mom. Adorable Widogast friendship to love story.
Relationships: Beauregard Lionett/Yasha, Jester Lavorre & Caleb Widogast, Jester Lavorre/Caleb Widogast
Comments: 22
Kudos: 179





	1. What hell have I gotten myself into?

**Author's Note:**

> Worte this when I stayed up watching way too many romcoms but I honestly like where it is going. Still unsure how many chapters it might be though.

Jester runs into Beau’s job at the college bookstore. Almost tripping over all the boxes spread around the room. She frantically searches till finally finding Beau walking out of the back room with another box of textbooks. Jester runs up to her nearly running straight into Beau, which would have resulted in all the books in Beau’s hand tumbling to the floor. Though knowing her excitable friend very well she holds out her hand to stop her before impact.

“Beau! Beau! I need your help, I got myself in a bit of a situation.”

Beau turns around, eyes on a hyperventilating Jester. Jester is fidgeting with the hem of her flowy blouse as she waits for Beau’s response.

“Jessie please tell me you didn’t try to flirt with the TA again. I know you swear Fjord was flirty with you but like I am pretty sure he’s banging his advisor, Professor Avantika” Beau can almost hear the disgruntles look in Jester's face with the mention of their old professor.

“No no no, I learned my lesson on that already. It about mama, she’s coming to visit next week.”

A hint of confusion falls onto Beau's face. Jester adored when her mother visited them, she couldn’t see why Jester was having such a meltdown right now.

“Why would that be a bad thing Jessie we all love it when your mom comes to visit. I mean we really need to clean our living room when we get home today but other than that-”

Beau is cut off by Jester beginning to ramble. Her words becoming harder to follow as she increases her speed with every word as her voice drips with anxiety.

“I might have sort of kind of told mama I have a really cool, smart, handsome boyfriend. You know who is really into me and like might even love me. And like I do not actually have a boyfriend or even a boy that is remotely interested in me right now. But like it was never a big deal cause you know mama is always busy, so she never comes to visit anyway. Plus, it made her so happy that I was finding love. But now she’s flying in on Friday and its all going to come crashing-”

Beau covers Jester's mouth with the hand to get her to stop rambling, waiting for her to relax a bit before removing her hand.

“Okay so let me get this straight. You lied to your mom and told her you were in a relationship with this amazing guy that doesn’t really exist. Now your moms coming to visit and you’re afraid she’s going to find out this was all just a story you made up”

Jester nods looking at the ground embarrassed, “I really didn’t mean for it to ever get this far Beau, it all started off as a big misunderstanding. But then mama was so happy, you should have heard her. You know she loves young romance.”

“I know Jessie but that doesn’t change the fact that now we have to come up with a plan to explain why this amazing guy is mysteriously never around the entire time she’s visiting. How long is she even staying; a week, two weeks?”

“Three months, maybe even longer she’s opening up a new hotel here and she wants to be here while the finishing touches are being done……………. We can say he went to visit his parents somewhere, I told her he was a world traveler like me.”

“Yea I mean I guess that might work would still be awfully suspicious though. She comes in for three months and he just happens to be gone, I doubt your mom will fall for that.” Beau lets out a deep sigh. She starts to place down the aisle tossing her keys in the air while trying to figure out how we are going to pull this off.

“It’s not like mama knows much about him. She just thinks he’s this really intelligent guy, who’s like super charming, but also really down to earth and a bit shy-”

Beau gets lost in thought as she paces the aisle trying to come up with a full proof plan to make it through this visit. Suddenly she hears her coworker and nerdy best friend helping another student find a textbook. She peers through the bookshelf to see her friend trying to push his messy ginger locks out of his face as he read the boy’s syllabus. He wasn’t ugly by any means just a bit unkempt especially during textbook time at the bookstore. He was a full-time student with two part-time jobs so most days he looked terribly exhausted. Coming to work in the same old black t-shirt and an oversized hoodie. Though she went to high school with him and remembers how nice he can look when he puts a little effort in.

“Hmmmmmm. Jessie, did your ever tell your mom what this new boyfriend looked like?”

Jester shakes her head, “Not in detail no, she just knows he’s supposed to be very handsome.”

A smile grows across Beau’s face, “I think I might have found a solution to our problem”

Jester jumps up excitedly, “Really?!”

Beau looks back at where her coworker has gone back to stalking shelves then back to Jester. “Yes, give me a minute. I am about to cloak out for my break in a few minutes. Why don’t you go buy us some lunch and I’ll meet you at our usual spot in like 20 minutes?”

Jester smiles and nods, “Alright sounds good, Salad? Sushi? Cupcakes?”

Beau lets out a chuckle, “Surprise me”

With that Jester skipped off to go gather their lunch leaving Beau to march her way over to her distracted coworker. She comes up to him as he’s running his hand through his beard trying to figure out were one of the books goes.

“Beauregard you wouldn’t happen to know where this Earth Science textbook is supposed to go. I could have sworn we used to stock them here.”

“I think Essek moved some of them to the next self over cause they didn’t fit after them new Chemistry books came in yesterday when he was on shift”, Beau points to the beginning part of the next shelf over.

“Ah, very well I shall go put it over there then”, walking past Beau books in hand.

“So Widogast, you know my cute friend with the blue hair that comes to visit all the time?”

Still stocking the shelves, he nods his head slightly.

“Ja. She is your roommate is she not umm I think Jester’s her name if I recall?

“Yes, Jester, the ball of sunshine who comes barging at all hours of the day while you and I are barely getting by with our 3 cups of coffee.” Beau can see a small smile form across his face.

“Ja, she is uncharacteristically chipper for someone who literally never drinks an ounce of caffeine”

“Yup you got to wonder where she gets all that energy from. Anyways her and I need a really big favor.”

“What kind of favor?” Beau can see he is a bit thrown off by the request but intends to hear her out.

“I need you to pretend to be Jester’s boyfriend while her mom is visiting” She doesn’t mean to but her lack of social skill makes it come off a little more awkward than intended. 

“Ummm huh?” He turns around to face her, confusion and disbelief written on his face. “I am confused”

“Okay, so Jess might have told her mother that she had this like super awesome boyfriend that’s like incredibly handsome and stuff. But in reality, it was all made up and he doesn’t exist. So, I was hoping you could do me a solid and pretend to be her boyfriend for a bit. I mean come on she’s cute, not like it be too much of a torture to spend lots of quality time with a pretty girl. Plus, you did theater in high school; I know your good at improv. I promise we'll make it up to you somehow Caleb.”

Caleb beings to rub his neck nervously, “I would think you would have better options than me, Beau. You're trying to impress her mother for god sacks I think I would be quite the disappointment. I am not exactly model status or anything”.

Beau shakes her and places her head and hand on his shoulders, “Don’t sell yourself short. I know you look like a bit of a mess right now but we both know you can look way better than this.”

Caleb smirks a bit, “Is that a compliment I hear Beauregard?”

She can’t help but laugh, “Don’t get used to it. So, is that a yes?”

“I don’t know Beau I have a lot on my plate right now. If I am not in a class, I am here working with you. If I am not here, I am babysitting Luc for Veth. If I am not doing that I am studying to keep up with my classes. Plus; I am still looking for a third job, money’s been really tight lately since my car broke down.”

“Oh, come on Caleb we really need your help. I will even take over watching Luc for you and you can keep all the money. Jessie just really needs our help; she doesn’t want to disappoint her mother. I’ll even help you pay to get your car fix, just please help me out here.”

Caleb looks a torn but eventually gives in to the pleading, “Ja, fine I’ll do it. Though I don’t know how thrilled Jesters going to be that I was the only one you could find to do this. Last time she and I talked she called me stinky and told me I should take a bath.”

Beau tries to hold in her laugh but fails, “I mean can you blame her Caleb you haven’t smelled the freshest in the past few months. If there’s one thing Jester lacks that’s a filter.”

Caleb looks down at his clothes, I mean yea he had not showered in a few days but in his defense, it had been a week at most. He thinks at least. And yea he had worn this shirt for the third day in the row, but it was comfy, and he was always running late in the mornings. He wants to blame his recent lack of appearance on school and work but while that is part of the reason he knows it really goes deeper than that.

“Ja, your right I have really let myself go I guess.” Caleb holds an aura of sadness to him but tries to brush it off. Beau tries to comfort him with a pat on the shoulder but is unsure if it is really helping or not. “So how long am I going to have to pretend to be her boyfriend for exactly?”

“At minimum 3 months”

“3 Months ?!?”

“What can I say Jester’s mom has business in the city if anything that should help so she won’t be constantly around.”

“I guess. You owe me, Beauregard.” Caleb points a finger at Beau.

“I am literally just asking you to spend time with a pretty girl you been wanting to get to know anyway. Does not seem like a bad day to be Caleb just saying…… Well I’ll be on break; I promised Jessie we would have lunch. Plus, I got to tell her the plan so see you in like an hour.” and with that Beau walks out of the bookstore.

Caleb leans against the bookshelf and slides himself down to the floor. Placing his head in his hands trying to figure what the hell just happened.

“What the hell have I gotten myself into?”


	2. Cayleb?!

**Summary for the Chapter:**

> Funny what a good shower and shave can do.

Caleb was a bit nervous walking up to Jester’s and Beau’s townhouse. This place was far fancier than anywhere he had lived making him feel a bit out of place. He had been outside many times before but never had really gone past their porch. He felt may he was a bit early, it was barely about to turn 1, and Jester’s mom wasn’t arriving at the airport till 7 pm. Though Beau had brought up that it might be smart for them to meet earlier so they could get their story straight. He took a deep breath and rang the doorbell. He hears jester yell through the door.

“It’s open come in”

Caleb opens the door making his way into the house it was just as stunning. He was meet with a large sparking chandler. He sometimes forgot the Beau came from a wealthy family. In his defense, she was not one to show it much and hardly ever took much money from her father anymore. He on the other hand was far from wealthy. He only got the opportunity to attend the fancy private school he met Beau at because his uncle Ikithon had offered to pay. Stating he did not want a young man of such intelligence to have it wasted amongst squalor and poorly funded programs. Caleb takes another deep breath before making his way through the entrance to the open living, dining, and kitchen area. Jester is laying on the couch watching TV. When she hears him get closer, she sits up to look up at him. A grin forms across her face as she looks him over.

“Omg Cayleb you look so handsome!”

Caleb could feel his face turning a bright scarlet. In her defense, he did look miles better than any way she has ever seen him. His once scruffy beard replaced by a freshly shaven face, his skin looking smooth and supple bringing out his chin dimple. His dirty oversized hoodie and old jeans replaced with a freshly washed dark pair and a charcoal Henley shirt, sleeves folded up to his elbows. Suddenly out of his oversized, ill-fitting clothes he no longer looks scrawny instead very toned, his arms being a bit distracting if you ask Jester. To top it all off his once cow licked greasy ginger hair was freshly washed softly pushed back a bit but still allowing the curls to show through.

“Umm well thank you, Jester, you look very pretty as well” Caleb awkwardly stampers out.

She did look very pretty though wearing a black long-sleeved skater skirt dress. The V-shaped neckline accentuated her bust quite nicely. Her chest displaying a beautifully intricate Sapphire necklace. She stood up and for the first time Caleb realizes how short she truly is, it had been harder to tell with her usual over the top shoe choice. She walks up to him looking up at him as she grasping his chin softly with a huge smile still plastered on her face.

“Ooooo look you even have a cute little dimple on your chin Cayleb.”

He only darkens in color as suddenly his very way of the attentions she is giving him. Beau comes walking in from a room down the hall. Drenched in sweat from what Caleb can only guess was one of her intense workouts. She had a grin on her face as if she had been watching them for a while and just barely decided to make her presence known.

“Looks like you guys got the flirting down.” Beau stares a bit more intently at Caleb, “Damn Widogast, I haven’t seen you look so boyish since we were in high school. You went from looking like you were in your thirties to looking your actual age for once”.

Jester pulls Caleb onto the large L couch, sitting herself down next to her feet tucked under her. Grabbing a plate from the coffee table full of baked goods and placing them in front of him.

“Would you like some Cayleb? They’re really good, I am personally partial to the bear claws but honestly no matter what you pick you can’t go wrong.” She dances around a bit in her seat waving them in front of him.

He can help but smile at her giddy nature, picking up one of the bear claws, tearing off a piece and placing it in his mouth. It really is very lovely, he can see why she seems so endeared to them.

“I made us some tea; I hope that’s okay. I know you and Beau prefer coffee, but we ran out yesterday.” Jester nervously picks at the sleeves of her dress, rocking in place a bit.

“Tea will be just fine, thank you Jester” Caleb picks up the brightly colored mug to take a sip.

“Thank you for agreeing to help me by the way. I know this all must seem a little unorthodox. I swear I don’t usually lie to people like this, especially not to mama. She just accidently understood I had a boyfriend which made her so happy. So, I was too embarrassed to tell her that she had miss understood me. Then suddenly it had gotten terribly out of hand and now I am here begging for your help to cover up my mistake. You must think I am so stupid.” Jester is unable to keep eye contact with him instead opting to look down at the sleeve she’s been playing with.

“I don’t think your stupid Jester. You were just trying to protect your mother’s happiness.” He rubs her arm a bit in an effort to comfort her.

It seems to help as she straightens herself ups a bit letting go of the sleeves she had been playing with. “Thank you Cayleb.” She takes a deep breath. “Shall we begin then?”

He places what’s left of his bear claw down on a napkin, “Ah ja. So first off what exactly have you told your mother about this mysterious boyfriend, I’ll be playing.”

“Well I told her you were extremely handsome, and we clearly got that covered”, Jester brings her hand up gesturing to him. He awkwardly smiles still not comfortable with the concept of being considered attractive.

“Ummm I told her you were very smart. I did not tell her what you were studying, just said you did very well in your classes. So that should be good, well just tell her whatever you are actually studying. What are you studying Cayleb?” Jester looks up at him intently waiting for an answer.

“I am actually studying to become an English professor, though I hope to write a novel one day,” Caleb answers shyly still with the same awkward smile.

“Ooooo a professor, that’s pretty hot Cayleb. Going to have me be your little teacher’s pet hmmmmmmmm” She teases him suggestively wiggling her eyebrows.

He lets out a small chuckle and quickly tried to change the subject, “What about you Jester what are you studying?”

“I am actually majoring in Art. I am a really good artist just so you know. Like that painting we have hanging on the wall, I did it” she pointed to a picture behind her, it’s a realistic painting of her and beau in front of a beach.

“Wow you made that, that’s amazing Jester. I thought it was a photo when I first walked in. The detail on it is amazing” he wasn’t even trying to flatter her he was truly in awe of her talent.

Jester blushed a bit but continued, “Thank you…anyway umm I also told her you were very charming”

“Hmm well that’s where we might have an issue if you haven’t noticed I am extremely awkward”

“You’re not that awkward Cayleb, I think you're actually very charming. Plus, I said you were a bit shy so that should help a bit so you don’t have to talk a lot” she flashes a reassuring smile at him.

He smiles back at her suddenly aware that she had scooted closer to him after showing him her painting. Spending time with her now he couldn’t understand how she didn’t have a real boyfriend. She was extremely pretty and adorable. Easily the sweetest most personable person he had ever meet.

“I am sorry I called you stinky last time we talked” Jester looked down at her lap.

“It’s okay, in your defense I really was in the need of a shower. I looked and smelled like a reck.” He gives her a reassuring smile. “Now back to more pressing matters. Anything else I need to know”

“Well, mama thinks we met when I was studying at the library waiting for Beau’s shift to finish.”

“Ja, okay good to know”

“Umm, she thinks your well-traveled, which shouldn’t be hard according to beau you’ve traveled quite a bit too. The accent is a nice touch, it's German right?”

“Ja, it is. Do you think it would help if we used terms of endearment?”

“Oooo yes, Cayleb! That’s a great idea! Do you have any in mind?

“Well, I typically would always refer to you as Blueberry in my head when I would see you visit the bookstore. Ummm there’s also Liebling which means darling in my native tongue.”

“Those are perfect, I love them”, the glimmer in her eye is so distracting Caleb doesn’t even realize Beau has made her way to the living room.

“Also heads up, Jester's mom is like really swell off” Beau calls out as she throws herself on the couch making a money motion with her hand.

“Oh, yea mama makes a lot of money she owns a lot of really fancy hotels.” Jester nods in agreement.

Caleb tenses up, his only real interaction he had with the wealthy, that wasn’t at the Academy, was with his uncle. To call his uncle a prick would be an understatement. He looked down at the poor as if their financial struggles somehow made them lesser than him. He was merely a horrible man who laundered money and took advantage of the vulnerable. He called himself an investor if you ask Caleb his nothing more than a conman. This scarred Caleb a bit he didn't assume her mother would be a horrible person or anything he just feared feeling out of place. He also didn't want to embarrass just with his lack of financial stability. I mean he was a grown man doing a babysitting job normally reserved for teenage girls because he couldn't afford to keep himself afloat with just his bookstore job and financial aid. 

“Should we not let her know how broke I am then”

“What? No Cayleb mama doesn’t care if you come from money or not. She only cares that you are a good person. Oh, and that you'll take care of me.”

“Oh alright.”, Caleb looks down a bit sheepishly.

Beau gets up and starts heading for the door car keys in hand, “Well I'm off to watch Luc so Veth can go to work. Have fun you two. Oh and you might want to practice a kiss or two, wouldn’t want that to be what blows your cover.”


	3. I didn't mean it that way

**Notes for the Chapter:**

> Hope you guys enjoy :)

Caleb took a deep breath as they drove Jester’s car to the airport. The smell of cinnamon and sugar filling his lungs. Her car felt warm and inviting compared to his old broken down one currently at Orly’s shop. He has never had such a pleasant experience driving through rush hour traffic. Though he did find himself a bit anxious whenever a car got uncomfortably close to her really expensive car, unsure what he would do if he got into a reck in it. The car ride was going quite well, Jester was a unique passenger to have in the car. She was singing along to the music, dancing around, occasionally trying to convince Caleb to join in. He swears at one point he even sees her throw in the macarena. Caleb found it to be a pleasant distraction for his anxiety. Jester can see the small smirk Caleb is currently trying to suppress. Jester lowers the music just enough so they can talk.

“You’re going to love mama Cayleb.”

Caleb releases the smile he had been holding back. “I am sure I will Jester.”

“I must warn you though mama can be umm a little forward and eccentric.”

Caleb can’t help but chuckle, “Really Blueberry, I would have never guessed with how reserved you are.”

Jester’s mouth hung open in shock, “Are you teasing me Cayleb?”

“What? Me? Never.”, he had the biggest grin planted on his face.

Jester liked these random pockets of Caleb’s personality showing, most of her interactions with him in the past few years had been extremely brief. Jester had grown to know Caleb as Beau's extremely reserved friend who went to the academy with her. She would hear random stories from Beau about their shenanigans or simply see him in a quick passing glance. He would awkwardly wave hi from a distance when they ran into him on campus, always hiding in one of three oversized hoodies.

The longest conversation they ever really had was back when they had just started at the university. Jester had decided to join Caleb, who had been eating alone at a bench in the courtyard. He looked like a mess, hair greased like he had not showered all week, his clothes equally as dirty and worn. She remembered Beau telling her how Veth and him had been having trouble with their water at the new house they were renting. She had felt bad and offered to let them use one of the showers in the townhouse till they got their water back. She thought it would make him happy but instead, he was confused and upset. Eventually just quietly apologizing for being a mess and walking away before finishing his food. She thought she must have annoyed him like she had most people she tried to befriend.

“You know Cayleb I was starting to think you didn’t like me.” Bringing this up made her nervous, causing a slight fluctuation in her voice.

This caught Caleb’s attention, looking at her from the corner of his eye, “Why would you think that?”

“Well, every time I show up somewhere you disappear. Like literally the second I walk into the bookstore you run to hide in the back.” She is now fidgeting with the ends of her curls a hint of sadness in her voice.

“Oh,” Caleb let out a sigh he felt bad now, his insecurities had made Jester feel like she did something wrong. He never thought his aloofness would hurt her.

Jester felt the shift in the air as Caleb deflated, she quickly beings to ramble trying to turn the conversation back around.

“It’s okay if you thought I was annoying a lot of people do. Beau says I am an acquired taste. I know I am like super loud and never know when to shut up ever and-”

Caleb is quick to cut her off before she can go on any feather “Nein, I do not find you annoying Jester.” Letting go of any pride he had left he continues. “I actually umm actually avoided you because I was embarrassed.”

Jester turns her head to look at Caleb who was staring out at traffic. “Embarrassed?”

He lets out a heavy sigh. “Ja, embarrassed”

“Why though?”

“Well umm you see we never really got the chance to talk while I was in high school with Beau. Then umm when you came up to me on our first week of college I thought, oh cool this is my chance to get to know her. But then you called me stinky and told me I needed a bath. And I was oh ja that’s right I am just dirty stinky Caleb that nobody really pays much attention to.” Caleb winced as each word fell out of his mouth.

Jester’s face went through a world of emotions starting at confused and ending at mortified.

“Omg Cayleb. I am so sorry I didn’t mean it like that I swear. Its just Beau had told me how you guys were having a problem with your water because you were renting a new house. And like I though- ” Jester sinks down in her seat trying to hide her shame.

Caleb takes a hand off the wheel and places it on Jester's shoulder. “It’s okay Jester really it was my fault for taking it wrong.”

Jester turns to Caleb with a sad face “Oh, Beau is right I always stick my foot in my mouth”

“I mean if it makes you feel better, she’s not one to judge I can remember numerous times where she’s done the same thing.”

“Told people there stinky.”

Caleb lets out a chuckle, “No, put her foot in her mouth, though I wouldn’t be surprised if she has done that too.”

Jester laughs, “That would explain why we almost got kicked out of prom”

“Are you sure that wasn’t because you road one of the school's horses into the gym?”

“I can neither confirm nor deny that. I can also neither confirm nor deny that I was responsible for the unicorn horns on top of all their heads.”

Caleb's smile grows as he remembers the story. He still kind of kicks himself for not going, Beau made it sound like quite the sight. Then again, he knew prom was no place for someone as depressing as him, he would have killed everyone’s fun.

Jester suddenly feels the car stop; she hadn’t even realized they had gotten to the airport already.

“Ready?”

“Of course. Wait! Wait!”

Before Caleb can question her, she loops their arms together, letting herself lean into him a bit. Taking in the warm aroma of his cologne, he was quite warm for not wearing a coat. The afternoon showers had left a slight chill in the air that made Jester's hands ice. She looks up to see him smiling waiting for her next move.

“Now we can go find mama”

They find Jester’s mother sitting at the Bar with a tall gentleman Caleb can only assume is her husband, both in business attire. Jester's mother is mulling over a cocktail chatting with the man and bartender. The moment she spots Jester she rises from her seat with a huge, walking towards her daughter with open arms.

“My little Sapphire!”

“Mama!” Jester practically jumps into her arms.

Marion pulls her in for a hug before turning her attention to Caleb. “And you must be the man of the hour.”

Caleb walks up behind them ready to greet, “Caleb Widogast, what a pleasure it is to finally get to meet you and your husband Madam Lavorre

“Husband? Oh, you mean Bluud, he’s not my husband darling he is my personal protection.”

Jester playfully snickers under her breath just enough for only Caleb to hear, “Look who’s putting their foot in their mouth now.”

Caleb holds in a chuckle and quickly corrected himself, “My apologies for my assumption Madam Lavorre.”

“It's quite alright, you wouldn’t be the first to make that mistake and please call me Marion.”

Caleb gives her a charming smile, “As you wish.”

“My my aren’t you quite the alluring character, I can see why my daughter is so crazy about you.”

Jester is beaming watching her mother interact with Caleb.

“Oh, trust me I am nothing compared to the wonder that is your daughter. I am quite lucky she has even given me the time of day. Now please let me take your bags, we will lead you to the car you look quite exhausted.” With that Caleb slings her purse over his shoulder using his arms to grab her bag and begins walking them back to the car.

Marion’s smirk does not go unmissed by Jester who has now laced her arms with her mothers. Walking slightly behind Caleb, themselves being trailed by Bluud who is towing his and one of Marion’s bags as well.

As they are making their way Caleb stumbles a bit almost dropping all the bags. He is able to make a recovery though the awkward jagged movements it takes do not go unnoticed by the group trailing him. Caleb can feel himself turn an even deeper shade of red as Jester’s giggles hit him cementing the fact that everyone saw.

“Are you alright dear?” A playful, giddiness chiming through what would normally be a more concerning question.

Caleb nervously does his best to collect himself, “Oh ja ja, I am just fine blueberry.”

He can feel her playfully pinch his bicep as she continues to give him a hard time. “Your right, I know your super strong Cayleb.”

“That’s sad and funny at the same time”, Caleb mutters under his breath a slight chuckle escaping.

Marion watches from behind, enjoying the playful banter. She never really got to see her daughter interact with people that weren’t their servants or the Lionetts’. Jester’s entire childhood was restricted to their humble estate mostly. The only person who even dared take her into public often was her uncle Artagan. Marion herself hardly even went into public instead choosing to stay on their properties for most of her existence. This meant all of Jester’s adventures had always only been mere stories to her.

She had missed her daughter's presents dearly when she left off to college. She understood Jester was safe with Beauregard, but it did not break the fear that she had failed to prepare her daughter to interact with the world. Though it seemed despite the shelter life she had lived for her first eighteen years she had assimilated quite nicely. She was proud of these new bonds her daughter had made.

Marion’s thoughts melt away as she sees her daughter has somehow found a way to climb a walking Caleb. Now perched on his back as they near the parking lot. It seems to be weighing on Caleb slightly though its hard to tell if its truly from the newly found weight of Jester piggyback riding or the uncontrolled laughter she has caused from said piggybacking incident.

“Jester we’re going to fall.” Caleb struggles to get the words out between his laughter.

Jester firmly wraps her legs around his torso, “I have no idea what you're talking about Cayleb I feel quite secure.” Jester then proceeds to tickle his sides further.

Marion finds herself releasing a laugh before she decides she should put the poor boy out of his misery.

“Sapphire darling please get off of him, he is trying to walk”

Jester obeys releasing herself from Caleb. She purposely drops her smile pouting at both of them, head falling to admire the now asphalt floor. “I am sorry”

Caleb pauses for a moment, now standing directly in front of Jester, “You're fine Blueberry, I’d just like to get your mother’s things to the car in one piece. Something tells me breaking my Schwiegermutter’s things on the first day won’t make the most stunning impression.”

Caleb follows his statement by moving the hair out of Jester’s face, placing a soft kiss on her forehead. It tickles ever so slightly making a warm smile grow across her face replacing her pouting lips. They then continue their journey to the car.

Caleb drives them to the Lionett’s beach home, the place where Marion has arranged to stay for her time in the city. On there way there a heavy storm begins but they make it to the home fine and help them settle in for the night. They say their goodbyes and Marion begins leading them out of the house.

“Sorry I ruined your fun earlier my Sapphire though I’m sure you’ll find plenty of time to ride him later.” A suggestive smirk on Marion’s face.

Jester giggles at her mother’s comment, “Oh I will.” Giving her a suggestive eyebrow wiggle.

They are about to settle into the car when they hear Marion call out to them.

“Be safe you two”

Caleb smiles back to her and reassures, “Don’t worry I’ll drive slow”

“I didn’t mean on the roads.” Before either can respond Marion retreats to the comfort of the warm home.

The meaning of Marion’s words slowly hits Caleb. He can reluctantly feel his face turn a bright shade of red once more. Staring straight into the windshield watching the water fall on a slightly fogged glass. He can hear the echoing of Jester’s giggles as she settles into the passenger seat.

**Notes for the Chapter:**

> Thank you for reading:)  
> Please tell me what you think


	4. Ja, she really is isn’t she

**Notes for the Chapter:**

> Hope you guys enjoy :)

The slight showers of the afternoon had transformed into a roaring thunderstorm. Caleb couldn’t even see the car in front of him at certain points. Not to mention the numerous power outages among the city that made the drive take much longer than expected. They arrived sometime around midnight the house still thankfully having power. Veth’s car was already parked in the driveway as Caleb pulls Jester’s car up. They find themselves running to the porch as they are being assaulted by the storm. Veth quickly opens the door to find a drenched Caleb and Jester.

“Oh My God! You guys are soaked! Let me go get some towels.” Veth bolts down the hall to a closet grabbing as many towels as she can carry. Practically throwing them on to Caleb and Jester, starting to help them dry off, “You guys are going to catch a cold.”

Caleb stares out the main window watching the storm rage on, thunder and lightning striking the horizon. “Jester I can’t in good conscious let you drive home in this weather. I am sure Veth wouldn’t mind you spending the night.”

Veth’s eye double in size, “You were planning to drive home!! No! No! No! You are staying right here where it is safe.”

Jester joins Caleb in staring out into the storm. A larger lightning striking followed by an eerily close thunderous roar, causing Jester to jump back into Caleb’s chest. “Yeah Okay”, a tremble heard in her voice.

“It’s settled then, you will stay the night. Caleb get this poor girl some dry clothes.” Veth continues to dry off Jester.

“Oh, ja be right back” Caleb awkwardly stumbles down the hall to one of the bedrooms.

Veth turns her attention back to Jester, “Would you like some tea dear? Oh, and if you guys are hungry there is still plenty leftover from dinner.”

“Both would be nice thank you”

“Make yourself at home then I’ll go get that heated up for you”. Veth goes off to begin boiling some water, leaving Jester to wonder about the living area.

The house was cozy, many knick-knacks covering the shelves. A collage of photos displayed on the wall, in which Jester looked over intensely. There were no recent pictures of Caleb most were him in the early years of high school. The most recent photo of him being his graduation from the Academy. Jester knew pictures of Caleb were hard to come by if she was being honest Caleb himself was hard to come by. He was such a hermit sometimes then again so was she. 

Jester feels a soft tap on her shoulders that jolts her back to reality she turns to see Caleb standing in front of her dressed in a black v neck and sweatpants. A pile of neatly folded clothes in his hands as he wears a slightly nervous smile on his face.

“The shirt might fit you a bit more like a dress, but it was the best I could do. Umm, You can use my room to change, there’s a bathroom attached to it if you need it.”

Jester takes the clothes from his hand and begins to make her way to his room turning back for a moment, “Well if it fits like a dress, I might just have to embrace it.”

Jester closes the door behind her and is met with a warm smell of mahogany. His room was simple the cream-colored wall meshing well with the various shades of browns and oranges. The foot of a decent-sized bed was to her right, a large chest and door to her left. Straight ahead was a bay window draped in white curtains, an orange tabby sleeping on the seat. Jester could tell Veth was responsible for most of the décor, but she felt it captured Caleb’s essence very well.

Caleb at his core was a warm and charming person. She had seen it peak through a few times throughout the years, but today had been the most she had ever seen it. She laid out the clothes he gave her and began to strip her soggy wet clothes, taking care to throw them in the bathroom. She pulled over her head the grey tee shirt he had left her, which on her fell roughly a little above mid-thigh. She pulled on some a pair of box briefs and long black socks he had supplied her with, leaving the sweatpants on the bed. Evaluating herself on the mirror behind his bedroom door, before walking back out into the main part of the house.

Jester found Caleb and Veth seated at the dinner table. A plate of food placed at an empty seat for her to join. Veth places her tea down and gives them both a smile.

“So, besides the swim, you both decided to take. How was picking up Jester's mother?”

Caleb laughs, “I feel like decided is a very strong word.” Combing through his still quite wet hair.

Jester takes a sip of her tea before joining in, “Mama loved Cayleb. You should have seen him Veth he was so charming and made mama laugh.”

Veth smiled, “I never doubted he was going to make a good impression on your mother, Caleb is a wonderful man.”

Jester nodded in agreement, “Yes he is very wonderful and charming. Might I even say dashing.”

Caleb wanted to melt into his seat as Jester and Veth continue to compliment him. He could feel his face becoming redder and redder with each word.

Veth reaches across the table to touch his face, “Ugh and it so nice to see you clean-shaven.”

Jester reaches out to tap his chin, “I would have never known you had this adorable butt chin if you hadn’t.”

Caleb stares intently at the two women fondling over him, oh how he just wanted to shrivel up and die.

A small half sad smile crosses Veth’s face, “It’s just really nice to see you take care of yourself again Caleb.”

Veth words hit Caleb hit him like a ton of bricks. Veth had been with him through some of the roughest years of his life without complain. She supported him through everything. He hadn’t really thought about how it must have affected her all these years.

Dinner seems to fly by and Veth excuses herself from the table to rest. Caleb leads Jester back to his bedroom to get settled. Grabbing a pillow off his bed heading towards the bay window for a blanket.

“I’ll be in the living room if you need me. Feel free to grab another blanket or sweater from the closet if you get cold. Umm warning Frumpkin might try to snuggle you at night though he tends to like to sleep on the window. Um-”

“Don’t be silly Cayleb we can share the bed”

“I wouldn’t want to make you share a bed with a stranger.

“We’re not strangers Cayleb, I’ve known you since we were 13. I watched you graduate; you went to my first art show. I know you always take the blueberry muffin from the breakfast I leave you guys at the bookstore; I even know you make really funny jokes when you think people are not listening. You could argue we’re not close, but we are far from strangers.”

Caleb stares at Jester bewildered, he never realized how much attention Jester paid. She always looked like she was in her own little world doodling in her sketchbook. He can’t fight this strange urge to smile.

Jester returns his smile, “Now come on I’ll even put a pillow between us if it makes you feel better.”

Caleb reluctantly sits on the opposite side of the bed. Jester lays down and pats the pillow next to her. Caleb places the pillow in hand between then before joining her in bed.

“Goodnight Cayleb”

“Ja Goodnight Jester”

Caleb is awoken by the repeated ringing of his phone. He goes to reach for it but is held back by a weight on his chest. He looks down to see a mop of blue hair nuzzling itself further into his chest. He does his best to stretch out to reach his phone without disturbing her, bringing it back to him to answer.

Caleb struggles to get words out through his grogginess, “Ja Hello.”

Beau responds in a heated panic, “I can’t find Jester and I am freaking out dude. She’s not in her bedroom. Her cars not in the garage. She-”

Jester slowly is woken up by the commotion, “Cayleb go back to sleep it’s too early”

Beau pauses for a moment processing what she just heard, “Widogast did you-”

Caleb’s drowsiness fades as his eyes go wide with panic, “No! No! Nooo!”

“Give me the phone” Jester pulls the phone from Caleb’s hand and begins talking to Beau. “No, I did not have sex with Cayleb. I am sorry I didn’t text you; I didn’t mean to make you worry. Yes, I am sure. Even if I did would it really be that bad? Okay. Okay. I get it your only asking cause you care about us. Okay. Okay. Byeeeeeeee”

Jester then hands Caleb the phone and returns to her position clung to his chest. Caleb just lays there in shock for a few moments trying to process everything. He found himself playing with her hair as she slept. She was warm and comforting on a cold fall morning, the smell of vanilla tickled his nose.

It had been years since he had awoken to someone in his bed like this. It was a sense of intimacy long gone from his life, yet this felt dangerously inviting. He could feel her breath fall and rise against him; the soft sound of her breaths entranced him. For the first time in many years, he found himself yearning for more of this, which seemed ridiculous considering how much he had shunned everyone away. Maybe the years of therapy Veth encouraged him to go through had finally paid off. Maybe it had to do with how comfortable Jester made everyone around her feel. Or maybe it was because he could tell himself none of this was real, they were merely acting like one does in a play. They were just doing this to please her mother, a guy like him would never have a chance with a girl as lovely as Jester Lavorre.

Caleb looked down at the sleeping Jester cupping his hand around her face gently. Jester was right they weren’t strangers they had spent the past ten years together in a group of misfits. This was becoming a bit too much for Caleb and he found himself getting up and leaving a pillow to replace him. He didn’t want to get attached to something that might not be real.

Jester awoke to the realization that she was now alone in the bed. She starts to wonder if she had just imagined she was laying on Caleb’s chest. Though she thinks back to the night, remembering the steadiness of his heartbeat soothing her in her slumber. It had drowned out all the harsh thunder and crashing from the storm, leaving her feeling safe and warm.

Jester had lived an extremely sheltered life in comparison to most of their friends. Marion had homeschooled her all the way up to the end of high school. Till the age of 5, her only friend was her Uncle Artagan who would take her out to the stores and parks. Beau was brought into her life so that she would have a friend her age to play with. The Lionett’s found comfort in their typically stand-offish daughter finding a friend in Jester. Beau had introduced Jester to all her schoolmates, but Jester still spent much of her time in solitude. Her mother had told her how dangerous it was to get close to people. Though Jester had always wanted to be close to someone. Part of her felt empty because of it.

Jester is thrown out of her thoughts by a pair of eyes lurking over the bed. She makes eye contact with them, “Hello?”

“Oh no Frumpkin she found us, run”, a little boy around six pops up and runs out the door.

Jester laughs and gets out of bed slowly following behind the boy. She is greeted with the sight of breakfast laid out on the table. Caleb is reading a book and Veth is cutting up Luc’s pancakes.

“Mom! Mom! Uncle Caleb has a girl in his bed!”

Veth can’t help laughing at her son’s enthusiasm, “Yes I know Luc I saw them come in last night”

“Is she your girlfriend Uncle Caleb?”

Caleb struggles to figure out how to answer this, “Ummm-”

Before he can answer Jester responds, “Yes, I’m his girlfriend. You must be Luc it’s nice to finally meet you, I am Jester.”

Caleb turns to see her standing in the doorway a smile planted on her face. He watches her walk up to the table and join them. This all looked too natural like it was real.

“Good morning Veth. Good morning Luc. Good morning honey.” Her voice was like music to his ears.

She brushes Caleb’s hair out of his face and began enjoying her pancakes occasionally holding a piece up for Caleb to eat. This brought a smile to Veth’s face, Caleb typically didn’t eat breakfast always opting for just black coffee. She enjoyed seeing him get roped into the meal as Jester would not move her arm till he took his piece. She even snuck additional pieces of pancake on to Jester’s plate when he wasn’t looking.

Luc goes up to Caleb and whispers in his ear, “She’s really pretty and sweet.”

Caleb lets out a sigh through his half smile, “Ja, she really is isn’t she”

**Notes for the Chapter:**

> Thank you for reading!  
> Please tell me what ya think:)


	5. Could have fooled me

Jester goes into the kitchen to help clean up the mess from breakfast. Veth collects the rest of the plates from the table, leaning over to whisper at Caleb. She had a soft smile and a joyful warmth in her eyes.

“She’s good for you.”

Caleb lets out a solemn breath, “This is not real Veth.” It hurts more than he’d like to admit but he knows he shouldn’t let himself fall for the illusion. If he were to buy into it like the rest, he would only end up more hurt in the end.

Veth arches her eyebrow in a very suggested manner as she grabs the last plate. “Could have fooled me.” With that Veth makes her way to join Jester in the kitchen.

Caleb looks up from the pages of his book to watch as Jester and Veth chat away as they do the dishes. Jester gently swaying side to side as they scrub. Her hair still lightly holding on to the curls from the night before, his shirt seemingly fitting so perfectly as a dress. A small smile grows across his face as he whispers to himself, “Could have fooled me too.”

He finds himself watching their playful banter instead of going back to his book. Chuckling at the expressive way Jester moved as she told Veth stories from her interactions with the rich and snobby. Veth, who’s guilty pleasure was the Housewives’ of Nicodranas, was fully enthralled in the gossip. Jester catches Caleb staring at them out of the corner of her eye, playfully winking at him. Caleb quickly covers his face with his book as he feels his face turn a bright shade of red. Though not quick enough for Jester not to notice. Eventually, they finished and Veth made her way to go check on Luc and get on with her days plans. Jester still had not come out though, probably making herself some of the left-over pancakes or something.

Roughly fifteen minutes later Jester comes up to him tapping lightly on his book to get his attention. He looks up to find she has a fresh cup of coffee in her hands and a beaming smile across her face.

“Veth told me that you usually like a second cup and probably weren’t going to come into make it since you wouldn’t want to bother our girl talk.” She slides the cup from her hand over to him on the table. “So, I thought I’d make it for you.”

The same dumb smile from earlier pops up on to this face. “Ja, thank you.” She truly was going to be the death of him.

Jester plops herself down on a chair next to him, tucking her feet under her. “Soooo, Cayleb…”

“Ja?” Caleb places his book down on the table to give Jester his full attention.

“Mama invited us to have dinner with her and the Lionettt’s tomorrow at this really fancy place downtown.”

“Ah well we have plenty of time to prepare then. What is the dress code for this um fancy place?” A slight nervousness found in his voice. Caleb did not have many fancy clothes and certainly wasn’t in the position to be purchasing such things.

“Decently formal, I’ll have to wear a long dress and you’ll have to wear a suit.”

“Ah I see, I don’t own many suits Liebling.” Caleb nervously drinks his coffee. He hasn’t had many nice clothes since he left his uncle's business. Then again, he also hasn’t really found the need for them in recent years either.

“Oh, don’t worry about that Cayleb I already called in a favor with one of my mom’s designer friends and he was over the moon about dressing us for the evening. He said we could come in around two to try on our outfits so he can make any alterations if needed.”

Jester said this so casually like they were just going to the mall or something. He suddenly felt very hyper-aware of the money that Jester came from. She was a Lavorre, youngest of one of the wealthiest families in the Menagerie Coast. She never had to want for anything. She never had to live without anything. Damn, what was she doing with a guy like him? Jester can see the internal conflict manifesting in his eye.

“Are you okay Cayleb?”

His eyes wander back to Jester’s. “Oh, ja I am fine I guess umm I just kind of forgot how wealthy you are. You don’t act like the snobby girls I went to school with so it’s easy to forget.”

“Ugh, I hate those girls. They’re the type of people who think money buys happiness and let me tell you that’s far from the truth.” The ending of Jester’s sentence seems to come out more somber than intended but she does her best not to show it on her face. 

“Well I guess you be glad to hear in the thirteen years of knowing you, you have never once come off like those girls.” He offers her a reassuring smile.

“That’s a relief sometimes I think most people only see me as a dumb heiress.”

“You are far from dumb Blueberry. Most of the girls from the academy would have killed to be as smart as you. You know how many of them had to practically drive themselves crazy just to get into our University, while you didn’t even break a sweat.”

“And to think some of them still had to have their parents pay their way into college.”

Caleb bursts out into laughter. “Ja, that’s true.”

Jester smiles at Caleb trying to regain her composure from laughing at her own joke. “He’s expecting us by two so we should start getting ready we still need to stop by my place so I can change.”

Caleb nodded and with that, they prepared to leave on their endeavors for the day. After Caleb gets dressed, they find their way to Jester’s so she can change. Lucky for the both of them it seemed Beau was out, probably out getting ready for tomorrow evening with Yasha. After this morning’s wakeup call they both really weren’t ready to face her. They made their way to meet Marion’s friend at his design studio downtown. It took up a few floors of one of the nicer warehouse buildings in the area. Jester walked in like she knew the place by heart.

“Gilmore!” She cheered as she walked up to a very handsome man, dark long hair pulled back out of his face making it easy to see his charming smile.

“Jester darling, it’s so great to see you” He looks over her shoulder, eyeing Caleb who is cautiously walking in behind her a few steps back. “My god you didn’t tell me you were dating a model.”

Jester giggles softly, “He’s not a model”

“Well he should be, look at him.” He turns Jester around to face Caleb with him. “I mean I know you must look at him all the time, who could blame you with a face like that. But look his bone structure alone is to die for. I’ll give you the number for the agent I work with. He can be in my next show.”

Caleb is awkwardly staring at the ground not sure what to do with all the attention that is suddenly upon him. Jester can’t hold in her giggles as she teases Caleb. “What do you say Cayleb want to be in his next show?”

Caleb looks up to see Gilmore smiling at him, Jester right beside him looking like she’s enjoying every second.

“Umm, I don’t know about that. I don’t think I would make that great of a model. I don’t really have the confidence for that.”

“Oh, please the best way to build confidence is to get yourself out of your comfort zone. Just think about it, whatever you land on Jester has my number. Now come come we have outfits for you to try on.”

They follow him to find two outfits hanging on the clothes rack. Gilmore pulls them off and hands them to each of them.

“Go put them on I’ll be there in a bit to see what needs to be altered. I have a surprise for you two.” He points to two different privacy screens and sends them on their way.

They each try on the outfits and wait for him. He comes pins any ill-fitting areas then hands them each another outfit to try on. They both walk out to find the other dressed in some of Gilmore’s latest collection.

Jester glided out in a long flowing white sundress with her heels just giving her enough height for it not to touch the ground. The deep neckline and draping almost giving it a goddess-like feel. Her leg peaked out of the side of a long slit that went dangerously high up her leg.

Caleb followed in a pair of nicely fitted navy trousers complemented by a fitted white button up arms rolled up to his elbows. Warm brown oxfords and belt tying the look all together. The outfits seemed so simple, but he knew one of them alone easily costed more than his paycheck. He found himself completely in aww of Jester though as she is spinning in front of the mirror admiring her dress. 

Gilmore smiled at her reaction, “I thought you might like them.”

Jester gives him a cheerful smile, “I love but this is too much at least let me pay you for them.”

“Oh, please your mother pays me well enough to be your personal stylist, this one's on me.”

Caleb stares at himself in the mirror. He hasn’t dressed like this since he was under the care of his uncle. He admires the expensive fabric and leathers; he easily looks like one of the trust fund babies he went to school with. Jester comes up to him posing herself next to him in the mirror.

“Well don’t you look cover worthy. I hope you’ll still remember all of us little people when you get all famous.”

Caleb laughs at Jesters teasing, “I haven’t even said yes to his offer Blueberry.”

“I know I know it's just fun teasing you.”

Caleb instinctively pulls her in for a hug, freezing at first that he might have crossed a line. That fear fades though as she tightens her grip on him. Suddenly the lines between acting and reality feels blurred, but he tries to remind himself that while he may look the part he is far from a man who deserves her. Yet somehow as they now found themselves walking down the streets of downtown hand in hand, he can’t help but let his imagination wander. Did he actually have a shot with Jester Lavorre? No that’s silly, right?

They decided to stop downtown for a quick bite at a café. Getting refreshing tea and colorful macarons they made their way to a table inside. Jester chatted away about how her latest art peace was going showing him sketches and other miscellaneous drawings. He talked to her about the latest book he’s been reading and even promises to lend her one from his collection. They were seated inside a beautiful courtyard garden and the soft sound of birds filled the air. Caleb feels like he is dreaming. His friend of many years was flirting with him, and not just to see him squirm in his seat. This felt like a real date. It’s as if all worry leaves Caleb’s mind, without a second thought picking a white orchid from the garden and places it in Jester’s hair

“Orchids symbolize love, beauty, and strength… I don’t think there is a more perfect match for you.” He lets his hand rest on the side of her cheek.

Jester can feel herself blush at his words, a smile lighting up her face.

“You are a gift from the gods Liebling. I am just an awkward and clumsy nerd who’s lucky to even be sitting here with you. I am afraid I am going to mess this up somehow.”

“I don’t know you seem to be doing pretty well if you ask me.” Jester mischievously arches her eyebrow at him. They are only inches away from each other now, he can feel her soft breath hitting his lips. He can see she’s nervously biting her bottom lip. He wants to kiss those lips. It feels like they're both about allow themself to melt into each other when.

“Bren?”

Caleb froze, he knew that once warm Zemnian voice. He and Jester break apart, he turns to see a woman with a side shave. She was gorgeous, dress as though she might have come from brunch. Caleb gets up to almost inspect her presence, now standing directly in front of her leaning back on the edge of the table. Jester feels intimidated by her presence and familiarity with Caleb.

“Astrid? Um, how lovely to bump into you.” Jester could hear the harshness in his voice, he was far from pleased to see her.

“It really is, I haven’t seen you in ages.” Astrid steps closer to Caleb challenging him a bit.

“Well, we’ve certainly gone our different ways.” He stares down at her left hand where a large engagement ring is placed on her hand. “How’s Eodwulf?”

“Umm well, actually he has taken your place in your uncle’s company.”

“It wouldn’t be the first time he’s replaced me would it.”

Astrid tracts his eyes back to her engagement ring covering it with her other hand self-consciously. “You know I guess he just has the drive you lost many years ago. Maybe if you didn’t make it habit abandoning those who rely on you, he wouldn’t have to constantly pick up the slack.”

“Ja sicher, ich bin derjenige, der dich verlassen hat.” He tenses up, discomfort and anger clearly growing on his face.

Jester realizes she’s seen enough; rising from her seat she walks over to meet them, placing herself in Caleb’s arms in hopes of comforting him. He gladly accepts her presence finding himself rapping an arm around her. Jester is in no way close to fluent in Zemnian, but she knows that Caleb is on the defense.

Astrid looks annoyed by the interruption, “May I help you, Bren who is this”

“Oh, ja this is my girlfriend-

“Genevieve Lavorre”

Caleb is caught a little off guard by Jester using her full name, he knows she prefers being referred to as Jester. Astrid’s face is priceless though as she freezes, Lavorre was a name very few on the Menagerie Coast could claim.

“Lavorre as in one of the most influential families in Nicodranas Lavorre” Jester can hear the peaked interest in Astrid’s voice.

Jester smiles coyly, “Actually, I believe you mean the most influential family in Nicodranas.”

“How did you-?” Astrid looks confused. She doesn’t understand how Caleb has found himself in the company of such a powerful family.

Jester can see the mental struggle in Astrid’s eyes, cutting her off before she can question further. “Oh, we bet through Beauregard Lionett. You might have known her she attended the Academy with Cayleb. We’ve been acquainted for quite some time and when I found out he was single a few years back. Well, I would have been stupid to not jump on the opportunity. He’s smart, charming, and handsome. I’d be kicking myself right now if I were the dumb soul who-” Jester pretended to have a moment of realization, “Oh… it’s okay I am sure this Adolf fellow is nice as well.”

“Oh”

“Yes, well it was lovely meeting you and all but we have very important places to be right my love.” Jester looks up to Caleb pushing back his hair with her hand.

Caleb looks enamored by Jester, smiling at her as he gives her a small nod, “Ja, your right blueberry.”

Astrid stares at them a bit dumbfounded by Jester’s effect on Caleb. They gather their stuff and make their way to the car. Jester trying to hold in her laughter still from Astrid’s face.

“Jester Lavorre I didn’t think I would ever see the day”

“What?”

“You just flaunted your status of being a Lavorre.”

“I know it felt icky but damn it felt good to put that girl in her place.”

“Thank you by the way.”

“It was nothing really Cayleb, you’ve done it for me some many time.”

Caleb looks at Jester confused. “What do you mean?”

“You don’t let people tear me down. You’ve done it for years and I feel like I’ve never really had a chance to repay you for it.”

“I think you give me too much credit blueberry.”

Jester shakes her head. “No, you’re really great Cayleb” She combs her hand through his hair. “It just makes me sad that everyone seems to be able to see it but you.”

Caleb stares at her dumbfounded. “I don’t really have much to offer.”

“We’re not asking for the world Cayleb were happy to just take you. A really smart, extremely sweet guy who we know we can always rely on.”

**Notes for the Chapter:**

> Translation
> 
> Ja sicher, ich bin derjenige, der dich verlassen hat.
> 
> Yeah sure I'm the one who left you


	6. Peace and Yasha's Intuition

**Notes for the Chapter:**

> Not sure how I feel about this chapter but oh well I am already halfway through the next chapter and I think this one at least ties it together well enough.

They end up finishing the errands a lot earlier than expected and decided to go take a nice walk on the beach. Holding their shoes in their hands they make their way through the, surprising not crowed, beach. Jester had brought a small bag of beach essentials that apparently, she always has in her car. No one seemed to be paying much attention to them, but Caleb felt a little silly walking around the beach in such nice clothes. It felt like they were all watching them. He didn’t think Jester looked out of place though, she looked stunning skipping around in her white dress. He follows her down a secluded path at the edge of the beach that leads to a secret area.

This was Jester's favorite place in the whole entire world. No one really came to this side of the beach, so it was tranquil and quiet. She would come here and spend her day painting and drawing in her journal. It was her sacred space to escape to when she felt overwhelmed or needed a good cry. She never brought anyone here, till today. She’s not even completely sure what drove her to drag Caleb here. Caleb was the most removed friend from the group, but she was the second. She felt he might appreciate the spot unlike most who overlook it.

Jester laid out a blanket and place her shows down. Caleb set himself down on the blanket as Jester made her way to the water. Lifting her dress to not get it wet she dance and splashed through the water. Caleb chuckled to himself, he felt like he was in a romcom. Somehow an incredibly dorky guy like him had gotten a makeover and was on a date with a girl terribly out of his league. He finds himself taking out his phone and recording her graceful dance moves. She seems to catch on making cute poses in his direction.

“How do I look, Caleb?”

It simply just slips out from his lips. “Beautiful Schatz.”

This seems to make her blush as her smile seems to grow larger, ducking her head down a bit. Suddenly Caleb feels a tap on his shoulders, he turns to see a woman slightly older than him. She probably in her 30’s, ginger curls falling around her face.

“Would you like me to take a photo of you two?”

Before Caleb can even respond Jester runs up, “Yes please.” Handing her Caleb’s phone and dragging him into the water.

The woman smiles as she takes photos of the two. Caleb pretty sure Jester going to cause them to fall in the water. They finish their little in prompt to photo session and Caleb goes to retrieve his phone from the woman.

“Thank you. I am sorry if we bothered you.” Caleb looks and realizes the woman is holding what looks like an empty black ceramic vase.

“It’s fine. I typically just sit here and sulk, this was actually a very welcome surprise.”

Caleb can see a sadness built up in her eyes. “Are you okay?”

“Yeah. Umm, it’s just been a bit hard since-” Her voice cracked, and she can’t seem to get the words out. It pains her too much to bring it up.

“Since?”

The woman looks out at Jester who is still dancing around in the ocean. “Sometimes we forget how precious time is. You feel like you a god and nothing can defeat you till you find yourself falling off the cliff and reality sets. Don’t hold back on loving someone, you never know when the worlds going to take them away from you.”

Caleb joins her in looking at Jester, he can feel her words hitting him. Ever since the passing of his parents he had restraint himself from enjoying the finer things in life. Not in terms of money or even fancy things, though if you asked, he hasn’t had many of those recently either. But in the company of friends and the enjoyment of the smaller things in life. He had closed himself off from the greater world to sulk in his grief and misery. Only really going out with them after hours of Veth and Beau pulling at him to join them. Even when he was out, he didn’t really talk mainly just sat in the background and watched the rest of them have fun.

He turns back to ask her a question but fins she has disappeared. Suddenly he feels Jester jump on to his back. Somehow configuring herself into a piggyback position, resting her chin on his head.

“Caleb, can you please send me the photos?”

Caleb chuckles a bit, “Yes Blueberry.”

Caleb loses his balance and they fall onto the blanket laughing. Jester finds herself snuggling into his chest. Caleb takes a deep breath as he takes in the moment. This really did feel like he was dreaming.

"Do you know that women blueberry?"

She shakes her head a bit then stops, "No, well yes. Every so often with this really fancy black raven-colored urn. She sits at the edge of the water and talks to it saying she, sorry but she can’t find it in herself to let go yet.” Jester takes a breath. “The was empty today though so I guess she might have finally let go.”

Caleb reflects on the talk he had with the woman. She was trying to protect him from hurting himself. It’s like she knew he was holding himself back from letting this weird thing with Jester. He has not let go of past. He’s held on to, dwelled on it endlessly. He was no a man of faith by this did weirdly feel like some sort of otherworldly influence trying to jolt him in the right direction.

“Jester, why did you bring me here?”

Jester looks down at her hands nervously, “I don’t know this is my favorite place to go. I come her to read and draw when everyone is busy, and I don’t want to feel alone. It reminded me of you when your tucked away in you little reading nook. You said you liked it because it was were you were most at peace. This is my peace. I umm wanted to share it with you.”

Caleb can feel her tenses, so he squeezed her tightly to comfort her, “Thank you blueberry it’s wonderful.”

Jesters phone rings and she picks it up.

“Yasha says Beau and her have a favor to ask and if we can meet them for dinner to talk about it.”

Earlier that day

Yasha and Beau had spent all day trying to figure out a plan for tomorrow's dinner. They had gotten engaged three months ago but had forgoed telling anyone. Its not that they weren’t excited for everyone to know it's just they knew what would be coming everyone would want them to throw a huge wedding, something neither of them wanted. Beau paced rapidly in the in the living room of Yasha’s apartment. Trying to sort out a plan that would give them the best shot of not getting roped into the circus that would be a Lionett wedding. Yasha is laying on the couch looking at her a bit concerned.

“Why don’t we just tell them tonight about the engagement. That way tomorrow at dinner they can help us keep your parent in line.”

Beau looked at Yasha, “I don’t know Yasha they’ve been avoiding me all day after a semi uncomfortable phone call this morning.”

Yasha looks at Beau confused, “What do you mean?”

“I may have sort of panicked when Jester didn’t get home last night, so I called Caleb and found the reason I couldn’t find Jester was because she in Caleb’s bed.”

“Oooooh”

Beau dramatically gestures her hands in front of her “Exactly she suddenly spent the night at his house in his bed. This is a girl who’s never even had a proper kiss before.”

Yasha shakes her head admiring how much Beau cared for Jester. “Beau I know your protective of Jester but she’s an adult she can sleepover at a boy's place if she wants to.”

“But this is Caleb.”

“What’s so bad about Caleb if anything I think they're a really good match.”

“Really?”

“I mean yeah think about it. Jester would always flirt with him, and he’d get all shy about it. He always went out of his way to make sure she was okay. Jester was always obsessed with finding out what Caleb was doing. There were plenty of times when we were all out and you could find them in the back together hidden in their books. I think at one-point Caleb even told Jester she could have Frumpkin.”

Beau stands there trying to process all the information given.

“I know he can be a little reclusive but honestly so is she. I think they could be really good for each other. Just look at the past two days alone typically they’d both be locked away in the bedrooms all weekend.”

“I guess you got a point.”

Beau nods her head.

“Plus, Caleb’s has had a crush on Jester for at least a year now.” Yasha takes out her phone and begins to dial.

“What?” Beau looks at her in shock.

Yasha holds out her hand, “Shhh I am on the phone... Hey Jester, Me and beau have a favor to asks.”


	7. Wedding Bells and Secrets Spilled

**Notes for the Chapter:**

> Hope you guys enjoy :)  
> Next Chapter hopefully will be up in a few days along with hopefully two other multi-chapter works later this week and a one-shot.

Jester and Caleb make their way into Jester's townhouse. Yasha and Beau are already in the living room waiting for them both looking a little more serious than usual. Yasha gestures to the couch.

“Can you guys please take a seat.”

Caleb and Jester make their way to the couch. There’s a moment of fear that this might have just been a trap for Beau to confront them about this morning's phone call. Merely using Yasha as a way to catch them off guard but that’s all washed away though once Beau begins to talk.

“So, as you guys know Yasha and I took a trip a few months back. The one where we showed you all the cool stuff we had done.”

Jester and Caleb nod letting out a small breath of relief that this isn’t about the status of their relationship. Instead, being about the vacation their friends had gone on about extensively since their return

Beau continues, “Well umm one thing we forgot to mention from that trip was I asked Yasha to marry me and she said yes.”

Jester and Caleb stare at them for a moment trying to process everything be for practically lunging at them with hugs and congratulations. They all hug and celebrate before Yasha added to the conversation.

“Beau and I were hoping you would do us the honors of being our best man and maid of honor.”

“Of course, you guys.” Jester cheers pulling everyone in tighter.

Beau takes a deep breath and gets a bit nervous again, “Great now that we got the fun part out of the way we were hoping as our best man and maid of honor you would help us with something else.”

Jester makes a dramatic hand movement, “Joint Bachelorette party don’t worry we are on it right Caleb. We’ll give you the best bachelorette party ever.”

Beau laughs a bit before getting right on back on task. “I don’t doubt you will, but we had another request. You see my dad’s been a little gung-ho on the who wedding things recently and I know he really wants to throw this big lavish celebration but that’s just not something we want.”

Caleb finally speaks up, “So you want us to help keep everyone in control and stop them from turning this into a circus?”

Beau and Yasha unanimously nod, “Yes!”

Jester lets out a slightly concerning sound, “That’s going to be an interesting challenge.”

Caleb gives them a reassuring smile, “But we'll do what we can for our friends.”

Beau smiles as she hears Caleb. Jester makes her way to the kitchen.

“I think this calls for a celebratory drink.”

Grabbing some Champaign glasses from the kitchen cabinets and placing them on the counter. Caleb is a little thrown off at this at first because Jester here self is not much of a drinker. Jester brings out a nice bottle of champaign and pours out a glass for each handing them out to her friends. She raises her glass and they all follow suit.

“To my gorgeous friends I am so glad you found each other, you both deserve the world. Thank you for entrusting Caleb and me to be such an important part of your big day, we will do our best to make you proud. And if it all goes to shits, we’ll figure it out somehow.”

Caleb can’t help but laugh at Jester’s joke at the end, “Ja, we’ll figure something out.”

They all smile and take a drink absorbing the moment. Yasha sits and looks at the takeout menus on the counter.

“You guys want to order take out or something Beau has had me starving all day with her nervous pacing.”

Jester jumps up on a stole and looks through them with her.

“Ooo yes, we could get chines food.”

Everyone nods in agreement as they begin discussing orders. It doesn’t take long for the food to arrive all of them bring it into the living room to congregate and watch a movie. Beau pours them a few drinks as the night goes on, Jester ops grab a soda from the fridge. Though does take a sip of the drinks Caleb offers her to try. Mainly the sweet ones he thinks she might like. It is getting decently late when Caleb checks his phone.

“I should probably text Veth to come give me a ride home.”

Jester turns to him, “What? No Caleb don't be silly you can spend the night.”

“I wouldn’t want to be a bother taking over your couch for the night.”

“Don’t be silly Caleb it's fine. Plus, you can sleep in my bed with me tonight. The couch is fair to uncomfortable.” Jester absent-mindedly spewed out as she eats, he noodles.

Beau raises her eyebrows a bit, “Yea Caleb it's not like you haven’t shared a bed before. You guys seemed pretty cozy this morning.”

Jester and Caleb freeze, side-eyeing Beau as they think of a response. Yasha sees this and makes an internal decision to help, turning to Beau.

“I am getting pretty tired; do you mind if we call it a night and start getting ready for bed.”

Beau reluctantly agrees and they clean up their mess leaving Jester and Caleb in the living room. They watch a bit more before Jester turns back to Caleb. 

“If you want Caleb, we can get ready for bed and takes some snacks upstairs so we can watch the movie in bed.”

Caleb looks at her for a moment try to gauge what the best answer would be. “Sure”

Jester leads him upstairs to her room, the walls are a light grey except for one that has an incredibly beautiful mural painted on it. Her bedding is white with different shades of muted pink pillows and throws. Jester makes her way to her dresser taking out a black tee shirt for him and a navy pair of men’s boxes she bought to sleep in.

“I bought these because I thought they make really good pajamas they're a medium I think they will fit you.” She hands them to him, and he nods. “If you want to shower the guest bathroom downstairs has some soup you can use, Beau always leaves some for when she’s too lazy to come upstairs after a workout. I know you probably want to wash off all the sand from earlier.”

“Thank you, Blueberry.”

“Oh, and on your way back up could you bring the snacks pleasssee.”

“Of course, Schatz.”

They both go their separate ways to shower. After roughly fifteen minutes Caleb is out and dressed heading to the kitchen. Begins his search for all the snacks Jester had requested. He goes to the fridge to grab the soda and in shutting the door is meet by Beau. She has her arms crossed and a curious look in her eye.

“Why didn’t you tell me you have a crush on Jester?”

Caleb continues to search for the rest of the snacks avoiding Beau's eyes, “I didn’t think it was important to tell you about a crush I had on a girl who one tremendously out of my league and two I never had a chance with.”

“No chance with huh, says the guy who’s about to spend the second night in a row sharing a bed with his girl.”

Caleb just lets out a sigh, “I don’t deserve someone like her. She’s just doing this to impress her mother.”

Beau softens for a moment, “Impress her mother, Caleb do you see her mother anywhere. If this were really to impress her mother, she wouldn’t be spending every waking moment with you just cause.”

Caleb’s brain is analyzing what Beau is saying and tries to counter, “I am not the type of guy who ends up with a girl like her.”

“Jester is a smart, beautiful, wonderful woman from a powerful family; and I am just you guys poor nerdy awkward friend who comes with a ton of emotional baggage. I am not going to kid myself that I actually have a chance with her.”

Beau looks softens, “You're selling yourself short Widogast; you a great guy, an intelligent guy, who just got dealt a bad hand. We all have our baggage we carry around, Jester no different. I know your no stranger to that you’re always the one there trying to help her through it.” She pauses for a moment, “Ask her about her dad.”

Caleb looks at Beau in the eye for the first time during this entire conversation.

“Just give you self a chance man”

Suddenly they hear something fall in the hallway and rush over. They fine the vase my the front entrance fallen over and pick it up.

“It was probably just Jester’s dog he likes to run around the house at night sometimes.”

Caleb nods and heads upstairs, snack in tow to meet Jester. Beau’s words still taxing on his mind. He finds her pulling back the duvet, already having the side tables cleared for snacks. Jester starts making her way into bed smiling at Caleb patting the space next to her. Caleb joins propping up the pillow so he can sit up a bit. She ops to lay her head on his chest, neither really acknowledge instead slowly relaxing into it. The continue watching the movie in comfortable neither speak much except for random comments on a scene. Snacking on different chips and things here and there.

As time passes Caleb relaxes a bit more and finds himself sinking into the covers now jesters head more on his shoulder than chest. He can feel her breath tickle his neck ever so often. He would be living he said he didn’t like it. Jester is captivated by his warmth as she finds herself snuggling into him. Her hand making its way to come through his soft ginger hair. It was mesmerizing, he found him fighting the urge to show how much he was enjoying himself afraid it might startle her. Eventually, he finds a bit too hard as he lets out a soft barely audible moan. Jester hears this and is intrigued. She takes this opportunity to lean his head down to her. He stares into her amethyst eyes trying to figure out why she’s doing. Jester doesn’t give him the time pulling him in for a long passionate kiss. It takes him a few seconds to catch up before he kisses her back. She tastes like candy, and he can help himself when his tongue because her for entrance. She is more than happy to oblige letting his tongue in and pressing herself august him. Without even thinking he slides her on top of him, indulging himself in her presence. She is beautiful giggling as she flashes him a stupidly cute smile. Was he dreaming, did he fall asleep during the movie?

**Author's Note:**

> Thank you for reading:)  
> I'd love to hear your thoughts.


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